Trifluoroacetic acid → N-(3-(Aminomethyl)benzyl)-N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxybenzenesulfonamide

HRID 1889618Notes

Reaction equation

HRID 1889618 reaction equation
[C:1]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]([CH2:21][C:22]2[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=2)[CH2:25][NH:26]C(=O)OC(C)(C)C)[S:9]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[C:13]=2[OH:20])(=[O:11])=[O:10])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:26][CH2:25][C:24]1[CH:23]=[C:22]([CH:36]=[CH:35][CH:34]=1)[CH2:21][N:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:2][CH:3]=1)[S:9]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[C:13]=1[OH:20])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44594965tert-butyl 3-((N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Product 1

HCID 58531388N-(3-(Aminomethyl)benzyl)-N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxybenzenesulfonamideYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate (2.77 g, 4.41 mmol) in CH2Cl2 (15 mL) at rt was added TFA (6.8 mL, 88.0 mmol). The reaction mixture was stirred at rt for 4 h. It was concentrated and the residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The EtOAc layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo to give the product as a white solid (2.3 g, 96%). 1H NMR (DMSO-d6): δ 8.30 (bs, 1H), 7.61 (d, J=7.6 Hz, 2H), 7.59 (s, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.45 (t, J=7.6 Hz, 2H), 7.32 (m, 2H), 7.29-7.18 (m, 5H), 7.10 (m, 1H), 4.43 (s, 4H), 3.93 (s, 2H), 3.32 (s, 2H).

Workup

  1. concentrationIt was concentrated
  2. additionthe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
  3. customThe EtOAc layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28290f7a9a9b42c0b9b2896301474a6d
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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